You will find often find the less you are allowed to do with a computer the more user friendly it seems. This is hardly a coincidence. You need to make your decisions on how much inconvenience you are willing to take for freedom in computing. The first and most important step is to make these decisions deliberate. Perhaps after the keynote this necessity is clear.

I will detail my choices and my rationale. As Doctorow said, I avoid everything Apple. They have made DRM'd computing mainstream and I do not really want anything to do with them. When work makes me use a Mac (happens) then I use a very old second hand Mac Mini but have plans to switch to a Hackintosh. The best is if you can find a free hand down piece to make sure you are not fueling the Apple ecosystem even indirectly. And, I run OS X 10.7.4 because 10.7.5 comes with Gatekeeper and that software is simply not acceptable because it can limit the computer to only run Apple sanctioned applications. Another possible choice is to refuse work that requires a Mac -- I never claimed to be perfect.

Alas, the above decision makes you use Linux as your primary OS. Mind you: there are no good choices in the OS space. The "classic" Linux problems of laptops not sleeping, wifi, projectors are gone by now. Buying printers need a little care but most work.

Probably you want a smartphone and with the iPhone ruled out that probably means an Android phone. Pick one with an unlockable bootloader and install a custom recovery and a custom ROM. Consider as you install each free app on what are you giving up. I decided that using Google Maps is worth it for me but that's something everyone needs to decide for themselves and that's one of the hardest decisions. Practice healthy paranoia by sniffing your own traffic with tPacketCapture or a similar tool from time to time to make sure you know what's happening on the phone.

Speaking of traffic, make sure you can trust your router: buy one that is compatible with open source firmware and flash one. I was much afraid to make this step because I feared I will get another maintenance and/or stability nightmare but nothing like that occured. These days you can find a few with preinstalled DD-WRT even. If you choose one of these, make sure to email the manufacturer saying you've choosen their device because of the open source firmware. This perhaps will spur them to make more of the same. There are companies that purport open source compatibility but at the same time the small print says installing such violates warranty. Ask them why.

In eReaders, avoid the Kindle. I had a Kindle once -- the Paperwhite screen made me waver -- but no longer. These days I have a Kobo Aura HD for the beautiful screen of it. Make sure your eReader radio is off. Another of those convenience vs freedom decisions -- I very strongly prefer my device and my books being controlled by me and in turn I can suffer plugging the reader in to download a book or four. I recommend buying books from Barnes & Noble because their DRM is super easy to remove. Don't forget to email them thanking for this -- it's understandable they don't have the choice to sell DRM free books but at least they don't use the vile Adobe system many places use. Also, tech books at O'Reilly are DRM free, yay!